This invention relates to octahydropyridoindolobenzazepines.
Certain octahydropyridoindolobenzazepines are known from U.S. Pat. Nos. 3,373,168 and 3,457,271, assigned to Hoffmann-La Roche, Inc. Those compounds can be represented according to the above-mentioned patents by the following Formula (1): ##STR1## wherein R is a straight chain or branched alkyl having 1-7 carbon atoms.
According to the IUPAC 1957 Rules, the same compounds are represented by the formula: ##STR2## and are named 1,2,3,4,4 a, 8,9,14a-octahydropyrido[4',3' :2,3] indolo[1,7-ab][1]benzazepines. The IUPAC representation and nomenclature will be used herein.
The compounds of Formula (1) are said 1,2,3,4,4U.S. 8,9,14a-octahydropyrido3,373,168 and 3,457,271 to have antidepressant activity and to be useful antidepressant agents. These compounds are prepared according to the above two patents by reduction of the corresponding hexahydro compounds either with sodium in a mixture of tetrahydrofuran and liquid ammonia or with zinc in hydrochloric acid. The former method is preferred by the patentees since it gives higher yields.
U.S. application of C. D. Adams, Ser. No. 422,616, filed Dec. 6, 1973, which is a continuation-in-part of U.S. Application Ser. No. 325,352, filed Jan. 22, 1973 and now abandoned, discloses 1,2,3,4,4 a,8,9,14a-octahydropyrido[4',3':2,3]indolo[1,7-ab][1]-benzazepines which can be represented by structural formula 1 wherein R is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylmethyl, exo-7-norcarylmethyl, benzyl or phenethyl. The compounds of the application have a different steric configuration of the hydrogen atoms at the 4a and 14a positions from those of the above patents. The evidence is that the compounds of the application have the transconfiguration of the 4a and 14a hydrogens and that the compounds of the above patents have the cis configuration. The compounds of the application are made by reducing the corresponding hexahydro compounds with boron hydride/tetrahydrofuran complex in tetrahydrofuran or diethyleneglycol dimethyl ether, and are useful as CNS depressants analgesics.
U.S. Application Ser. No. 359,504, filed May 11, 1973, now U.S. Pat. No. 3,890,327, granted June 17, 1975, discloses trans-1,2,3,4,4a,8,9,14a-octahydropyrido]4',3':2,3]indolo[1,7-ab][1]-benza zepine and its use as an analgesic. This compound is sometimes hereinafter referred to as "the nor compound".